Owing to the rise in the volume of literature, problems arise in the retrieval of required information. Various retrieval strategies have been proposed, but most of that are not flexible enough for their users. Specifically, most of these systems assume that users know exactly what they are looking for before approaching the system, and that users are able to precisely express their information needs according to l aid- down specifications. There has, however, been described a retrieval program THOMAS which aims at satisfying incompletely- defined user needs through a man- machine dialogue which does not require any rigid queries. Unlike most systems, Thomas attempts to satisfy the user's needs from a model which it builds of the user's area of interest. This model is a subset of the program's "world model" - a database in the form of a network where the nodes represent concepts since various concepts have various degrees of similarities and associations, this thesis contends that instead of models which assume equal levels of similarities between concepts, the links between the concepts should have values assigned to them to indicate the degree of similarity between the concepts. Furthermore, the world model of the system should be structured such that concepts which are related to one another be clustered together, so that a user- interaction would involve only the relevant clusters rather than the entire database such clusters being determined by the system, not the user. This thesis also attempts to link the design work with the current notion in psychology centred on the use of the computer to simulate human cognitive processes. In this case, an attempt has been made to model a dialogue between two people - the information seeker and the information expert. The system, called Thomas-II, has been implemented and found to require less effort from the user than Thomas.